Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins
Chemical SciencePublished 1 January 2011
Miao Ding, Feng Zhou, Yun‐Lin Liu, Cuihong Wang, Xiao‐Li Zhao, Jian Zhou
Citations170
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TL;DR
A newly developed cinchonidine-derived phosphoramide 6b, simple and easily available, was identified as a powerful catalyst for the highly enantioselective addition of both unprotected 3-aryl and 3-alkyloxindoles to β-substituted nitroalkenes.
Abstract
A newly developed cinchonidine-derived phosphoramide 6b, simple and easily available, was identified as a powerful catalyst for the highly enantioselective Michael addition of both unprotected 3-aryl and 3-alkyloxindoles to β-substituted nitroalkenes to furnish the C3 quaternary stereogenic carbon center with an adjacent tertiary stereocenter in up to 21 : 1 diastereoselectivity and up to 99% enantioselectivity.
Keywords
Chemistry
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Chemistry - A European JournalOrganofluorosilanes as Model Compounds for <sup>18</sup>F‐Labeled Silicon‐Based PET Tracers and their Hydrolytic Stability: Experimental Data and Theoretical Calculations (PET=Positron Emission Tomography)
57 Citations2009Aileen Höhne, Lian Yu +7 more
A theoretical model of organofluorosilane hydrolysis, which correlates with the experimentally determined hydrolytic half-lives, is developed and permits the facilitated development of improved building blocks for the synthesis of novel (18)F-silyl-modified biomolecules for PET imaging.
Tetrahedron LettersEnantioselective addition of oxindoles to aliphatic α,β-unsaturated aldehydes
45 Citations2009Natalia Bravo, Ignasi Mon +4 more
A highly enantioselective organocatalytic oxindole addition to α,β-unsaturated aldehydes is reported, providing the corresponding adducts with good yields and with moderate diastereoselectivities.
Organic Preparations and Procedures InternationalEnantioselective Michael Addition Reactions
38 Citations2011Muniappan Thirumalaikumar
Tetrahedron AsymmetryAsymmetric construction of quaternary stereocenters by direct conjugate addition of oxindoles to enone
34 Citations2010Wangsheng Sun, Liang Hong +2 more
Chiral cinchona-based primary amine A was found to catalyze the asymmetric direct conjugate addition of prochiral 3-oxindoles with enones to afford 3,3-disubstituted oxindoles in good yields, moderate to high diastereoselectivity, and excellent enantioselectivities.
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